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2-Bromodibenzothiophene → 9-(dibenzo[b,d]thiophen-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole

HRID 1516997
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1516997
Br[C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[C:15]1([N:21]2[C:33]3[CH:32]=[CH:31][C:30]([C:34]4[CH:35]=[CH:36][C:37]5[NH:38][C:39]6[C:44]([C:45]=5[CH:46]=4)=[CH:43][CH:42]=[CH:41][CH:40]=6)=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC(C)([O-])C.[Na+]>C1(C)C(C)=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH:3]1[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[S:6][C:5]=2[CH:13]=[CH:14][C:2]=1[N:38]1[C:37]2[CH:36]=[CH:35][C:34]([C:30]3[CH:31]=[CH:32][C:33]4[N:21]([C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=5)[C:22]5[C:27]([C:28]=4[CH:29]=3)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:46][C:45]=2[C:44]2[C:39]1=[CH:40][CH:41]=[CH:42][CH:43]=2
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Komponenten

7

Edukt 3

HCID 2995082-BromodibenzothiopheneHCID 23676156Sodium t-butoxideHCID 593066299-Phenyl-9H,9'H-[3,3']bicarbazolyl

Produkt 1

HCID 584795889-(dibenzo[b,d]thiophen-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazoleAusbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
Katalysator
HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylKatalysator
HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of 2-bromodibenzo[b,d]thiophene (3.22 g, 12.24 mmol), 9-phenyl-9H-9′H-3,3′-bicarbazole (2.5 g, 6.12 mmol), and sodium t-butoxide (1.764 g, 18.36 mmol) in 100 mL of xylene was bubbled with N2 for 20 min. Pd2(dba)3 (0.056 g, 0.061 mmol) and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.100 g, 0.245 mmol) were then added, and mixture was then bubbled with nitrogen for another 20 min. The reaction mixture was refluxed under N2 for 24 h. The mixture was cooled and filtered through Celite. After solvent evaporation, the residue was coated on Celite and purified by column chromatography using up to 50% dichloromethane in hexane as solvent. 9-(dibenzo[b,d]thiophen-2-yl)-9′-phenyl-9H,9′H-3,3′-bicarbazole (2.1 g, 3.55 mmol, 58.1% yield) was obtained.

Aufarbeitung

  1. customwas bubbled with N2 for 20 min
  2. custommixture was then bubbled with nitrogen for another 20 min
  3. temperatureThe reaction mixture was refluxed under N2 for 24 h
  4. temperatureThe mixture was cooled
  5. filtrationfiltered through Celite
  6. customAfter solvent evaporation
  7. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-525eec47f4af44c2a6e48cc9f161a764
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08227801B2

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